


Without a Doubt

by Mishaltoe



Category: Supernatural
Genre: Multi
Language: English
Status: In-Progress
Published: 2014-04-11
Updated: 2014-04-11
Packaged: 2018-01-19 01:09:31
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,292
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1449721
Author URL: https://archiveofourown.org/users/Mishaltoe/pseuds/Mishaltoe
Summary: <blockquote class="userstuff">
              <p>Dean's a girl, Cas is freaking out and Sam's attracted to his sister, what?!</p>
            </blockquote>





	1. What have you done?!

**Author's Note:**

> Not finished, but getting there. :)

Crowley ran as fast as he could and he grabbed Sam’s arm as he swung behind Sam.   
“Get off me!” Sam shouted as he tried to walk away from Crowley .

“What’s the matter?” He asked.

“I accidentally spilled soup all over the  back of Squirrel’s car, he’s gonna kill me!”

Dean ran around the corner coming up in front of Sam with a snarl on his face.

“Hand him over, Sammy.”

Crowley made Sam’s shoulders shrug and in a mocking tone he said “Who? Crowley? There’s no one by the name of Crowley here just a big old moose, eh?”

Dean was unamused. “Crowley, get your ass over here, you son of a bitch.”

Crowley still protested, shrugging Sam’s shoulders again he said

“I have no idea what you’re talking about, it’s just a moose standing here!”

Dean stomped his foot and tried to push Sam out of the way, Crowley poked his head out from behind Sam and smiled at Dean.  
“Well, I’d love to stay and chat Squirrel, but demon work needs to be done.”  
“Oh no you don’t, you bastard.” He lunged at Crowley who pulled Sam in front of him, deflecting Dean’s lung sending Sam and Dean to the ground. Dean rolled off Sam.

“Don’t you dare try to smoke out of here, you dick, clean my car!” Crowley shook his head,.

“But darling, the King of Hell’s work is never done.” Dean kicked at him, missed and sent himself flying off the curb into a freshly chewed pile of gum. He growled, didn’t move, but growled.

“Sammy… I’m going to kill him.”

He finally stood up to face a laughing Sam and a laughing Crowley, who had a look of success on his face. Dean picked the gum off his forehead and felt his face go purple with rage.

“Just get your asses back to the damn car.”

He huffed and walked back towards the Impala. Castiel was cleaning the  soup out of the back seat because he too had to sit there. Dean climbed into the drivers side, he smiled softly at Castiel.

“Thanks, Cas.”

Cas smiled back, nodding as he took his place in the seat directly behind Dean.

“You’re welcome, Dean.”  
Sam and Crowley climbed into their seats, Sam in the front, Crowley in the back where the soup had been spilled. They exchanged a glance and rolled their eyes, both of them looking at Dean.

“Well now that the lovers have quarreled,” Crowley began, “Anyone mind telling me where the hell we’re going?”

Dean snarled, he turned the key, tapping his thumbs impatiently on the wheel.

“Sammy, where are we going?”

Just then Sam’s phone rang, it was Bobby.

“Hello? Hey, Bobby? You okay?”  
“You bet your ass I’m okay, are you okay? You guys busy? I think I got somethin for ya.”

Sam put the phone on speaker, Dean might want to hear this

“Alright, you there?”  
“Yeah Bobby.” They said in unison.

“There’s a case around Tennessee, Trickster by the looks of it.”

Castiel leaned up in his seat to listen.

“In a little town called Asa, there’s a lot of weird stuff going on, I think y’all oughta check it out.”

“Alright, Bobby.”

“Are your Hell bitch and Angel stooge still around?”  
Crowley mumbled under his breath “you used tongue, just remember.”

Castiel looked around before leaning up to Dean to whisper “What’s a stooge?”

Sam leaned back and gave Cas a “what did you just say” look.

“Yeah, Bobby, they’re here, and they can hear you.”

“Good then they can hear me say this: they ain’t going.”

Castiel and Crowley said in unison “And why the hell not?”

“You idjits will set off his radar the moment you step into town. You. Ain’t. Going.”

After ten or twenty minutes of protest Castiel and Crowley finally smoked out.

Before Sam could hang up Dean shouted “Hey, hey wait, Bobby!”

“Yeah?”

“Why… Why can’t Cas come?” He asked a little shakily

“Because your angel boyfriend will set his radar off and we’ll lose him, that’s why.”  
“He is NOT my boyfriend, Bobby, it was just a question.”

“Alright, kid, I have to go. Talk to ya soon.”

The boys kept driving, they’d be there in two hours tops.

“So, Dean, when are you going to tell Bobby that you’re gay?”

“When you admit you have a sympathy boner for Crowley.”

Sam rolled his eyes, nodding at Dean.

“‘Least I don’t have an angel up my ass…” he murmured.

“And the King of Hell ain’t in mine, is he?” Dean replied.

Sam put on a girly, sarcastic voice, “Ooooh! You’re right Dean, I’m gay, gay, gay for Crowley. He sold his soul for my pleasure!”

Dean rolled his eyes. “Alright, asshat, knock it off.”

***

 

Dean pulled up to a cheap motel 20 minutes inside Asa, he parked the car.

“Now sweetheart,” he began, “do you want to do the honors of getting our room key or do you want to go in together?”

He was referring to the fact that every time they went to a hotel, they were accused of being gay.

“No, no, sweetheart, I insist you follow behind, holding my hand and slapping my ass.” Sam winked.

Dean groaned, that usually got Sam to go in and get the key. He made his way up to the door of the hotel office, opening it, he walked up to the counter.

“One room, two beds, two keys, please.”

The guy rang up what he asked for, setting the keys to room 101 down on the counter. Dean slid his stolen credit card across the table, smiling.

“Thanks, man.”

He wandered out to the car, tossing a key on the front seat for Sam, grabbing his back and walking towards the room. Sam followed close behind Dean. As soon as they got into the room Dean flopped down on the bed.

“Sammy where the hell do we start?”

“Damned if I know, Dean.” He set his bag down on his bed, trying to sit down and relax. Dean’s stomach growled. “I’m hungry, Sam.”

“So go eat.”  
“Lets go get a beer, there was a crappy bar a few miles down the road.”  
“Alright, let’s go.”

They both made their way to the door, closing it behind them. Dean got into the front seat and shortly Sam followed, getting into the passenger seat. They drove towards the bar, Dean pulled into the parking lot and they both got out. Dean made his way to the bar, plopping down on the stool as he gave the bartender a sweet, flirty smile, he ordered a beer. Sam knocked on the bar a few seats down, ordering a shot of whiskey that he later followed with a beer. While Dean made eyes at the bartender, Sam sat down at a little table, looking around the bar for familiar faces. Dean turned to see where Sam went when he caught a glimpse of Gabriel, did a double take, and he had vanished. Dean hopped off the bar, running towards Sam, he slapped his arm.

“Sam, we have to go, now.”

“Why?”  
“Just have to. Let’s go. Now.”

Sam got up and followed Dean out of the bar and into the car, wondering why he was acting so weird. Dean knew that he and Sam couldn’t hide from Gabriel, at least, not anymore.

When they got back to the hotel, Dean jumped into the bed, crawling up under the blanket, with it over his head, he was exhausted.

“Sammy, wake me in a few hours, I need my rest.”

Sam nodded, he laid down on his bed.

About seven hours later Dean woke up, yawned and lifted his head. It was still dark in the room but he could make out Sam’s shape under the comforter. He made his way out of the bed after a while, trailing slowly to the bathroom. He rubbed his face before hitting the light, taking his first look in the mirror in the morning. His eyes were still a little groggy, but he looked at himself, but he wasn’t himself. He jumped back, hitting the wall.   
“WHAT THE HELL?!” He screamed.


	2. Uh, Oh!

Sam practically sprang awake  
“Dean? Dean what is it? Are you okay?”   
He made his way towards the bathroom, peaking in to see a shadow on the floor before getting a full view of Dean...he thinks.  
“Dean… is that… you?”  
Dean ran his fingers through his long, golden brown, wavy hair, then down over his hips, up his waist and finally he ran his hands over the new-found lumps on his chest.  
“Sammy… I… I HAVE BOOBS!”  
Sam rolled his eyes before laughing hysterically.  
“You’re a pretty girl, Dean.”  
“Shut up, Sammy!”  
Sam just laughed. Dean finally looked down, his eyes meeting the short, sheer, silky, black lingerie, and he yelped. Sam was too busy staring at Dean’s body to say anything so Dean ran for the bed sheet, wrapping it around himself like a dress. Sam started laughing again.   
“Put on some clothes, Princess, we’ve got work to do.”  
Dean nodded and went to his bag to get his clothes, but then when he unzipped the duffle, he sighed, kicking at the bed as he looked down to find leather mini skirts, white tank tops and a few brightly coloured cocktail dresses. Instead of his med-kit, he had a bag of make-up and instead of his regular tan boots or dress shoes, he had a pair of six inch black heels. He grunted.   
“That bastard, of course he did. Uh… Sam?”  
“Yeah, Dean?”  
“Can you go get me….something to wear?”  
“What’s wrong with what you’ve gotten in the bag?”  
Sam was curious why Dean had all of a sudden got weird and defensive over his duffle bag, so he went to grab it and Dean growled at him. He dodged Dean and took the bag.  
He laughed hysterically, holding a mini skirt up to his legs.  
“Mmm.. I don’t know, Dean, I might have to take this, my legs would look great!”  
Dean rolled his eyes and snatched the mini-skirt from Sam’s hand.  
“This isn’t funny, go get me some damn clothes!”  
Sam nodded and grabbed Dean’s keys and made his way out the door. Dean sighed, he couldn’t look like this in front of people, he felt like a damn hooker. He muttered various curse words under his breath as he looked at himself in the mirror. Thank God Cas isn’t here he thought to himself. He turned the TV on and sat at the edge of the bed. It’d had been ages since Dean actually sat down and paid attention to the television. The girly part of him had him watching Gossip Girl. He chuckled quietly at Dean Forester who looked so much like Sam did in years past.   
Dean sat there laughing and trying to relax when Sam rolled back up into the house, noticing that Dean was watching Gossip Girl, he quickly turned the TV off and swallowed hard, handing Dean something to eat. Dean crawled under the covers, eating as quickly as he could, when Castiel appeared in the corner. Dean pulled the blanket over his head and Sam laid down on the bed next to him.   
“Oh dear,” Castiel started, “I apologize, Sam, I did not know you had a female friend over.”   
Sam stood up, looking at Castiel and deciding to play this “female friend” thing, only because Dean pinched the inside of his leg with his newly long, sharp nails.  
“Where’s Dean?”  
Sam shook his head with a shrug, “I don’t know?”  
Castiel nodded before speaking quietly, “I’ll just call him.”   
Castiel called Dean’s cellphone, which lit up and began ringing on the table next to the bed, Sam sighed and threw the blanket off Dean.  
“He’s right here.”   
Castiel was confused, he looked down at the short, light brown haired girl on the bed, looking over her body.   
“Dean?” He said in a quiet and confused tone.  
“Y-yeah…?” He replied with a sigh as he wrapped one of Sam’s flannels around him. He was really red and blushed when he saw Castiel’s eyes wandering up his body in confusion and wonder.   
“Sam… Go get me clothes, since you seemed to have failed doing that the first time.” She nodded towards the food same brought instead of clothes. Sam nodded and proceeded out the door, giving Dean a smirk as he closed the door behind him.  
Castiel was still looking over Dean’s body, he thought to himself Dean… Looks different, good different, like really good, am I… attracted to Dean? I couldn’t tell him that…  
Dean had been studying over Castiel’s kind-of broad figure with her bottom lip in between her teeth, he hadn’t noticed how attractive Castiel actually was until just now, her eyes wandered up and down his body before he had the chance to speak.  
“So…” Dean finally spoke up, “Where’s Crowley?”  
Castiel shrugged “Fighting Abbadon in Purgatory still, he’s been there since you guys left. What’s wrong, Dean? You seem….different?”  
“I hate being a chick!” His sudden yell forced a stray piece of hair into his face which he tried several times to move from his face with no success. “And I especially hate this hair!”  
Castiel laughed quietly, moving the piece of hair from Dean’s face and tucking it behind “her” ear. “I think it is pretty.”  
Dean looked up at Castiel and blushed. “Well… thanks…” What the hell is happening?! He is your best friend and here you go blushing at him?! The hell is wrong with you?! Dean thought to himself before changing the subject.   
“Where did you guys go after you smoked out?”   
“Well… Crowley and I went back to the bunker to check on Kevin, who is doing fine, might I add, and then Crowley had to leave because of domestics in Hell talking about how the calvary was trying to escape Purgatory, so he went to put an end to it.   
“And you just came here?”  
“Yeah, to warn you about becoming a girl, but it’s as though I’ve missed my chance to warn you…” Castiel’s attention moved to the window as his face began to hint at pink tones.  
Dean looked awkwardly back at the TV, before speaking softly again. “How did you know he was going to change me into a girl?”  
“He’s been my brother for thousands of years, Dean.”  
“Right, right…”  
Castiel sensed worry and sat down on the bed next to Dean, his hand close to her thigh. Dean scooted away a little, he was nervous. Castiel pulled Dean into a hug suddenly, and Dean gasped.  
“Get off me!”   
Castiel laughed. “Dean, it is a hug.”  
Dean knew that they probably shouldn’t be in the hotel room by themselves much longer.  
“Where the hell is Sam?!”  
Castiel shrugged, “Probably on his way back, perhaps?” he said quietly.  
Dean stood up and looked at the door before pulling one of the mini-skirts on with a tank top. Castiel tried not to watch but couldn’t stop staring at Dean’s legs. Dean pulled the skirt down a little trying not to show too much skin to Castiel. Cas blinked, licked his lower lip and then nodded at Dean.  
“Cas, maybe we should go for a walk?”  
“Sure, Dean.”  
Dean made his way to the door, sighing sadly that the only shoes she had were heels. Castiel vanished for a split second before coming back with a pair of boots similar to Dean’s new size.  
“Perhaps these would be better?”  
Dean smiled brightly at Castiel.  
“You’re a life saver.”  
“I’ve been told, Dean.”  
She laughed quietly as she tied the boots on her feet with a smile.  
“Shall we?”  
Dean nodded as she opened the door, she knew Sam would be back soon and she didn’t feel comfortable being alone with Castiel, because of the way she looked and how he looked at her.  
She walked next to him and they exchanged random glances. She smiled sweetly at him and when they finished their circle around the hotel he pinned her by her hips against the doorframe.  
“Cas…” She whispered.  
“Shh..” He hushed her as his lips ghosted against hers.  
She started to pant quietly as he pushed his lips against hers, his hands trailing up her sides.  
When they broke the kiss, Sam had returned and was jaw-dropped staring at Dean and Castiel.  
Dean’s face flushed and Castiel didn’t know what to do so he disappeared.  
Dean smiled “T-thank you, Sammy.” she spoke in a quiet voice and she ran inside. Sam stared blankly for a minute and shook it off before he walked inside and handed her a bag with jeans and flannels and a bra in it. “This should do the trick” he muttered before he laid down on his bed and curled up. When Sam fell asleep, Castiel came to Dean with a smile. “Dean, Dean wake up..” he whispered quietly and she turned over to face him, she wasn’t asleep, she was too deep in thought to sleep.  
“Yes, Cas?” She whispered back, looking from him to Sam’s sleeping body over and over again.  
“I was wondering if you would perhaps be interested in accompanying me on a date of some sort? Such as dinner…”   
Dean’s face flushed, ‘Is my best friend asking me out on a date? oh my god, I can’t, this’ll ruin everything, EVERYTHING. Oh god, oh god what do I do?!”   
She smiled and looked into his eyes. “I...I would love to.” She whispered back, “tomorrow night?”   
“Yes”  
“Where are we eating?”  
“You’ll see, dress nicely”  
And with that, he disappeared.


	3. ....And So It Has Begun!

She thought for a long time if this was the right thing to do, she eventually fell asleep, but only when Sam was awake. He looked at her from his bed, puzzled at why Gabriel would turn her into a girl, and more importantly he was dumbfounded on why he was so shocked and jealous that Castiel kissed her. He always knew that Castiel and Dean had “a more profound bond” but he didn’t think it meant a bonding of their lips! He shook the thought and looked at her for a long time before he went to get food.   
By the time Castiel had returned, Dean had found herself a long blue dress and a pair of heels to match it. She didn’t know how on earth to do her own hair and makeup so she had hired a maid to do it for her. When Castiel came to the door, he knocked, which was weird for him because he never knocked, he just entered. Dean walked to the door, peeking through the hole and seeing it was Cas. Her face lost color and she stared at the door before she opened the door. Castiel’s eyes went wide. “She looks beautiful” He thought to himself as he looked her up and down. Dean felt really weird in a dress because she still had her male state of mind but she was loving the boobs.  
“Hello, Dean.”  
“Hey, Cas.”   
“Are you ready to go?”  
“As I’ll ever be.”  
She walked out the door and towards the car, very, very wobbly on her heels that were already starting to hurt her feet. Castiel stared her up and down as she walked. He laughed when she wobbled and he stared at her in a trance. She quickly snapped him out of it when she spoke “Are ya comin’, or do I have to drag you?”   
He shook out of it, “I uh, I’m coming, Dean.”  
He raced quickly to the passenger side of the car, not really used to sitting up front, but used to it enough. Dean looked at him and tilted her head slightly. “So...Where are we going?” She whispered quietly.   
“We are going to a French restaurant.” He said back with a small smile. He closed his eyes and he touched both sides of his seat and hers and they appeared in a parking lot for the French restaurant in the big city. “Shall we?”  
“Yes.”  
They entered the restaurant and were seated at a booth. Dean looked over the menu for a long time and tilted her head. “Hmmph.” She didn’t know what to order. The waiter came up to the table and his eyes rolled over Dean’s body, stopping at her chest.  
“Hey, eyes on your own paper, champ.” Cas muttered as he looked over the menu. Dean’s cheeks warmed up and her face turned pink. The waiter cleared his throat and smiled.   
“And what will you be having sir?”  
“I’ll tell you when I figure that one out.”  
The waiter huffed and walked away. He returned shortly and they both ordered their food. It wasn’t terribly interesting, just a few plates and a bottle of red wine. They made small talk, about her being a woman, about Gabriel and then about how awkward it is and what would happen if she became a man again.  
“Well, even if you did become a man again, I’d still want to be with you.”  
She nearly choked on her food. “Really?”  
“Absolutely!”  
She blushed and sipped at her wine again, leaving a lipstick stain on the glass. Castiel paid for the meal with money he stole from Sam and he helped Dean back out to the car, because she could barely walk on her own in those heels. When they got back to the car Dean kicked her shoes off and she held her hands tightly on the steering wheel, feeling a little tipsy from literally drinking a whole bottle of wine. Castiel zapped the car all the way back to the hotel. “Race ya!” Dean squealed as she opened the impala’s door and she started to run for the stairs. Castiel just laughed and he zapped himself to the door. “Does this mean I win?” He asked when she came up to the door to greet him.  
“THAT ISN’T FAIR!” She shrieked, “You used angel magic!”   
Castiel laughed and shook his head. “So?” He took a deep breath and pressed Dean’s back into the door, kissing her neck slowly, like he had seen before. The pizza man, what did the pizza man do? He thought to himself as he kissed slower. Dean’s eyes fluttered shut and she made a small, almost growling sound. She pulled on Castiel’s tie and kissed him hard on the lips. His hands traveled her hips and she put her hand on the doorknob before she muttered. “Oh, God, I hope Sam isn’t inside…” She twisted the knob and looked around.   
“Well it looks like the coast is clear, Dean.” Castiel decided before he picked her up and pressed her back against the wall, kicking the door shut. Dean’s eyes went wide, she’d never had sex this way, she was almost scared, and she sure as hell hadn’t ever been dominated. He ran his hands slowly up the slits of her dress, his hands along her skin made it cover in goosebumps and she leaned her head against the wall as her fingers tangled in Cas’s hair.   
Cas pulled Dean from the wall before he laid her down on the bed. She immediately decided she needed to help and she started pulling at his tie, ultimately, choking him, but he didn’t care. He got his tie off and she pulled the buttons on his shirt so hard they popped off and hit the floor. She blushed, embarrassed at her eagerness to have sex with her long, long, best-friend.   
Cas slowly started unzipping Dean’s dress and looked at her milky skin as it glowed from the moonlight coming from the window. When he finally got her dress off he looked down at her bare body, of course Dean wasn’t wearing underwear or a bra, what would the point of that be? He kissed from her neck down to her shoulder before she was attacking his belt her with now nimble fingers. She got his belt off and she set it on the floor before she pushed him down on his back and straddled his hips. She took his trousers off very slowly as her eyes went wide at the noticeable bulge in Cas’s white boxers. She licked her lips as she ran her fingers along his hardened length. “Wow…” She muttered before she slowly pulled the boxers down to reveal his length.   
Cas flipped her over again before he ran his hands down her silky, cream colored skin. He nipped her lower lip with his teeth gently, and then her neck before he very carefully bucked in. Her eyes went wide again, and then she started to pant. He started moving very slowly, given that the look on her face didn’t look like she was enjoying it. She moaned out quietly into the silent air. He started moving faster once he’d heard her moan. She gripped his skin tightly as her nails dug in. His eyes closed and he winced but he didn’t mind. He moved a lot faster than before as he broke into a sweat and started to pant a little on his own. By now Dean had scratched completely down his back and he couldn’t help but cry out as he felt himself already beginning to succumb to his own movements. Dean didn’t know how to feel, on the other hand, she wasn’t used to the one taking the cock. She moaned out loudly as she felt herself finish against his length, which ultimately coaxed him into his own finish with a loud cry coming from Castiel and filling the now silent air. He rolled over off of Dean and he panted loudly, staring at the ceiling.


End file.
